Fused Polycyclic Compound, and Preparation Method and Use Thereof

ABSTRACT

The present invention relates to the field of display technologies, and particularly to a fused polycyclic compound, and a preparation method and use thereof. The fused polycyclic compound provided in the present invention has a structure of General Formula IV. The structure of the compound has ambipolarity, and the HOMO level and the LUMO level of the host material are respectively located on different electron donating group and electron withdrawing group, such that the transport of charges and holes in the host material becomes more balanced, thereby expanding the area where holes and electrons are recombined in the light emitting layer, reducing the exciton concentration, preventing the triplet-triplet annihilation of the device, and improving the efficiency of the device.

RELATED APPLICATION

This application claims priority under 35 U.S.C. § 119(b) to ChineseApplication No. 201910353474.7 filed on Apr. 29, 2019. The entireteachings of the above application are incorporated herein by reference.

BACKGROUND Technical Field

The present invention relates to the field of display technologies, andparticularly to a fused polycyclic compound, and a preparation methodand use thereof.

Related Art

Organic light-emitting diodes (OLEDs) are a new display technology thathas more promising application prospects than liquid crystal displaytechnology, due to their fast response time, low energy consumption,self-lighting, wide color gamut, ultra-thin thickness, foldability andflexibility, thus receiving more and more attention.

In 1987, the first organic light-emitting diode (OLED) device wasinitially fabricated by Deng Qingyun et al. from the Eastman KodakLaboratory by means of vacuum deposition, which comprises transparentand conductive indium tin Oxide (ITO) as the cathode on which a diaminoderivative and tris(8-hydroxyquinoline)aluminum are deposited insequence, and comprises a magnesium/silver alloy as the anode material.Such a multilayer structure can reduce the driving voltage of the OLEDdevice, and effectively improve the charge injection at the interfacebetween the material molecules and the electrode, thereby improving thedevice performance and lifetime.

Compared with traditional technologies, the OLED devices have manyadvantages such as low driving voltage, high luminescence efficiency,high contrast, high color saturation, wide viewing angle, and fastresponse time. The current OLED device comprises a plurality of a holeinjection layer, a hole transport layer, a light-emitting layer, a holeblocking layer, an electron transport layer, and an electron injectionlayer, and suitable electrodes in combination. The plurality of layersis respectively formed of a hole injection material, a hole transportmaterial, a light emitting material, a hole blocking material, anelectron transport material, and an electron injection material. Alight-emitting layer of the OLED device that is fabricated by doping isadvantageous in the luminescence efficiency of the device. Therefore,the material for the light-emitting layer is often formed by doping ahost material with a guest material, and the host material is animportant factor affecting the luminescence efficiency and performanceof the OLED device. 4,4′-Bis(9H-carbazol-9-yl)biphenyl (CBP) is a widelyused host material with good hole transport performance. However, whenCBP is used as a host material, it is prone to recrystallization due toits low glass transition temperature, resulting in reduced performanceand luminescence efficiency of OLED devices. Moreover, an increase inthe molecular weight of the material can increase the glass transitiontemperature and thermal stability of the material, but reduce thetriplet energy level of the material at the same time, affecting thelifetime and luminescence efficiency of the device.

SUMMARY

An object of the present invention is to overcome the defects existingin the prior art that the host material in the light emitting layer haslow glass transition temperature, tendency to crystallization, poorthermal stability, and inability to have both good thermal stability andhigh triplet energy level.

To achieve the above object, the following technical solutions areadopted in the present invention.

A fused polycyclic compound has a structure shown below:

where the phenyl ring is attached to

at positions 1 and 2, positions 2 and 3, or positions 3 and 4 to form afused ring sharing the same side, in which “

” and “

” denotes the points of attachment, in which

when the phenyl ring is attached to

at positions 3 and 4 to form a fused ring sharing the same side, theGeneral Formula IV has a structure below:

when the phenyl ring is attached to

at positions 2 and 3 to form a fused ring sharing the same side, theGeneral Formula IV has a structure below:

and

when the phenyl ring is attached to

at positions 1 and 2 to form a fused ring sharing the same side, theGeneral Formula IV has a structure below:

T¹ is independently selected from a single bond, NR¹⁵, S, O, BR¹⁵, PR¹⁵,and C(R¹⁵)₂, in which R¹⁵ is the same or different, and is eachindependently selected from methyl, deuterated methyl, phenyl,deuterated phenyl, biphenylyl, deuterated biphenylyl, naphthalenyl, anddeuterated naphthalenyl;

at least one of T² and T³ is a single bond, when T² is a single bond, T³is S or O, and when T³ is a single bond, T² is S or O; and

R¹-R¹⁴ are the same or different, and are each independently selectedfrom hydrogen, deuterium, methyl, deuterated methyl, phenyl, deuteratedphenyl, and deuterated methyl substituted phenyl.

Further, R¹-R¹⁴ are the same or different, at least one of which is oneselected from deuterium, deuterated methyl, deuterated phenyl, anddeuterated methyl substituted phenyl.

Further, R¹-R⁴ are the same or different, and at least one of them ishydrogen; and/or

R⁵-R⁸ are the same or different, and at least one of them is hydrogen;and/or

R⁹-R¹⁴ are the same or different, and at least one of them is hydrogen;and preferably at least one of R¹¹-R¹⁴ is hydrogen.

Further, when T² is a single bond, T³ is S or O.

preferably, when T² is a single bond, T³ is S.

Further, the compound has a structure shown below:

Further, the fused polycyclic compound has any one of the followingstructures:

The present invention also provides a method for preparing the fusedpolycyclic compound.

When T¹ is selected from C(R¹⁵)₂, that is, the fused polycyclic compoundhas a structure of General Formula IV-1, and T⁴ is selected from ClC(R¹⁵)₂ or Br C(R¹⁵)₂, the preparation method comprises:

subjecting the compound of Formula (E) used as a raw material to acyclization reaction in the presence of a catalyst to obtain anintermediate compound (F); and coupling the intermediate compound (F) tothe compound of Formula (G) in the presence of a catalyst, to obtain thecompound of General Formula IV-1.

The route for preparing the compound of General Formula IV-1 is shownbelow:

Alternatively, when T¹ is selected from BR¹⁵, that is, the fusedpolycyclic compound has a structure of General Formula IV-2, and T⁴ isselected from hydrogen, the preparation method comprises:

reacting the compound of Formula (E) used as a raw material with thecompound of Formula (H) in the presence of a catalyst to obtain anintermediate compound (J); and coupling the intermediate compound (J) tothe compound of Formula (G) in the presence of a catalyst, to obtain thecompound of General Formula IV-2.

The route for preparing the compound of General Formula IV-2 is shownbelow:

Alternatively, when T¹ is selected from O, that is, the fused polycycliccompound has a structure of General Formula IV-3, and T⁴ is selectedfrom hydroxyl, the preparation method comprises:

reacting the compound of Formula (E) used as a raw material in thepresence of a catalyst to obtain an intermediate compound (K); andcoupling the intermediate compound (K) to the compound of Formula (G) inthe presence of a catalyst, to obtain the compound of General FormulaIV-3.

The route for preparing the compound of General Formula IV-3 is shownbelow:

Alternatively, when T¹ is selected from S, that is, the fused polycycliccompound has a structure of General Formula IV-4, and T⁴ is selectedfrom mercapto, the preparation method comprises:

reacting the compound of Formula (E) used as a raw material in thepresence of a catalyst to obtain an intermediate compound (K-1); andcoupling the intermediate compound (K-1) to the compound of Formula (G)in the presence of a catalyst, to obtain the compound of General FormulaIV-4.

The route for preparing the compound of General Formula IV-4 is shownbelow:

Alternatively, when T¹ is selected from PR, that is, the fusedpolycyclic compound has a structure of General Formula IV-5, and T⁴ isselected from hydrogen, the preparation method comprises:

reacting the compound of Formula (E) used as a raw material in thepresence of a catalyst to obtain an intermediate compound (L); reactingthe intermediate compound (L) in the presence of a catalyst to obtain anintermediate compound (M); coupling the intermediate compound (M) to thecompound of Formula (N) in the presence of a catalyst to obtain anintermediate compound (O); and coupling the intermediate compound (O) tothe compound of Formula (G) in the presence of a catalyst, to obtain thecompound of General Formula IV-5.

The route for preparing the compound of General Formula IV-5 is shownbelow:

Alternatively, when T¹ is selected from NR¹⁵, that is, the fusedpolycyclic compound has a structure of General Formula IV-6, and T⁴ isselected from nitro, the preparation method comprises:

reacting the compound of Formula (D) used as a raw material in thepresence of a catalyst to obtain an intermediate compound (P); andreacting the intermediate compound (P) with the compound of Formula (Q)and then the compound of Formula (G), to obtain the compound of GeneralFormula IV-6.

The route for preparing the compound of General Formula IV-6 is shownbelow:

Alternatively, when T¹ is selected from a single bond, that is, thefused polycyclic compound has a structure of General Formula IV-7, thepreparation method comprises:

reacting the compound of Formula (R) used as a raw material with thecompound of Formula (S) in the presence of a catalyst to obtain anintermediate compound (T); subjecting the intermediate compound (T) to acyclization reaction in the presence of a catalyst to obtain anintermediate compound (U); and coupling the intermediate compound (U) tothe compound of Formula (G) in the presence of a catalyst, to obtain thecompound of General Formula IV-7.

The route for preparing the compound of General Formula IV-7 is shownbelow:

where W is selected from fluoro, chloro, bromo, and iodo.

Further, the compound of Formula (E) is prepared through a methodcomprising:

nitrifying the compound of Formula (A) used as a starting raw materialin the presence of a catalyst to obtain an intermediate compound (B);coupling the intermediate compound (B) to the compound of Formula (C) inthe presence of a catalyst to obtain an intermediate compound (D); andreducing the intermediate compound (D) in the presence of a catalyst, toobtain the compound of Formula E.

The route for preparing the compound of Formula E is shown below:

The present invention also provides an electronic device, whichcomprises any one or a combination of at least two of the fusedpolycyclic compounds described above.

Preferably, the electronic device is any one of an organic lightemitting diode, an organic field effect transistor, an organic thin filmtransistor, an organic light emitting transistor, an organic integratedcircuit, an organic solar cell, an organic field quenching device, alight emitting electrochemical cell, an organic laser diode or anorganic photoreceptor.

Further, the electronic device is an organic light emitting devicecomprising an anode, a cathode, and an organic thin film layer betweenthe anode and the cathode, where the organic thin film layer comprisesany one or a combination of at least two of the fused polycycliccompounds described above.

Preferably, the organic thin film layer comprises a light-emittinglayer, and also any one or a combination of at least two of a holeinjection layer, a hole transport layer, a hole blocking layer, anelectron transport layer, an electron injection layer, an electronblocking layer, and a charge transport layer, where the light-emittinglayer comprises any one or a combination of at least two of the fusedpolycyclic compounds described above.

Preferably, the light-emitting layer comprises a host material and aguest material; and the host material in the light-emitting layercomprises any one or a combination of at least two of the fusedpolycyclic compounds described above.

The present invention further provides a display device comprising theelectronic device described above.

The present invention also provides a lighting device comprising theelectronic device described above.

The present invention has the following beneficial effects.

1) The fused polycyclic compound provided in the present invention has astructure of General Formula IV. The structure of the compound hasambipolarity, the HOMO level and the LUMO level of the host material canbe respectively located on different electron donating group andelectron withdrawing group, such that the transport of charges and holesin the host material becomes more balanced, thereby expanding the areawhere holes and electrons are recombined in the light emitting layer,reducing the exciton concentration, preventing the triplet-tripletannihilation of the device, and improving the efficiency of the device.

Meanwhile, in the structure of General Formula IV, by attaching thephenyl ring to

at the positions 1 and 2, 2 and 3, or 3 and 4 to form a fused ringsharing the same side, the structure of the compound is more highlyconjugated, more stable in the excited state, and more rigid, so thestability of the material is higher, which is beneficial to theextension of the lifetime of the device. Moreover, the particularstructure of the compound further facilitates the carrier recombinationregion in the host material of the OLED device to stay far away from theinterface of the light emitting layer to the hole or electron transportlayer, thus improving the color purity of the OLED device, avoiding thereturning of excitons to the transport layer, and further improving theefficiency of the device

The HOMO level and the LUMO level of the fused polycyclic compoundaccording to the present invention match those of the adjacent holetransport layer and electron transport layer, so that the OLED devicehas a small driving voltage. Furthermore, the compound, used as the hostmaterial in the light emitting layer of the OLED device, has hightriplet energy level and good thermal stability, which ensures theefficient transfer of energy from the host material to the guestmaterial and prevents the crystallization of the material molecules ofthe light emitting layer.

The compound of the present invention has a small difference between thesinglet (ΔE_(S1)) and triplet energy level (

E_(T1)), which promotes the reverse intersystem crossing of tripletexcitons to singlet excitons. Moreover, the high reverse intersystemcrossing (RISC) rate from the triplet state T1 to the singlet state S ofthe hot material can suppress the Dexter energy transfer (DET) from thehost material to the luminescent dye, promote the FÖrster energytransfer, and reduce the exciton loss generated during the Dexter energytransfer (DET), thus avoiding the efficiency roll-off of the organiclight-emitting device and improving the external quantum efficiency ofthe device, thereby achieving a high device efficiency.

2) Further, in the fused polycyclic compound provided in the presentinvention, R¹-R¹⁴ are the same or different, at least one of which isone selected from deuterium, deuterated methyl, deuterated phenyl, anddeuterated methyl substituted phenyl. By the use of deuterium havinglower potential well, lower vibration frequency, smaller amplitude andmore stable carbon-deuterium bond, the luminescence efficiency and theservice life of the organic light emitting device are improved. In thepresent invention, by defining that R¹-R⁴ are the same or different, andat least one of them is hydrogen; and/or R⁵-R⁸ are the same ordifferent, and at least one of them is hydrogen; and/or R¹¹-R¹⁴ are thesame or different, and at least one of them is hydrogen, thesubstituents on the structure

are not all substituted with deuterium, and the structure interacts withthe structure

which further facilitates the improvement of the service life of thedevice.

3) According to the organic light emitting device (OLED) provided in thepresent invention, the host material in the light-emitting layercomprises any one or a combination of at least two of the fusedpolycyclic compounds described above. As a host material in thelight-emitting layer, the particular fused polycyclic compound allowsthe transport of charges and holes in the host material to become morebalanced, thereby expanding the area where holes and electrons arerecombined in the light emitting layer, reducing the excitonconcentration, preventing the triplet-triplet annihilation of thedevice, and improving the efficiency of the device.

Moreover, the particular structure of the compound further facilitatesthe carrier recombination region in the host material of the OLED deviceto stay far away from the interface of the light emitting layer to thehole or electron transport layer, thus improving the color purity of theOLED device, avoiding the returning of excitons to the transport layer,and further improving the efficiency of the device

The HOMO level and the LUMO level of the fused polycyclic compoundaccording to the present invention match those of the adjacent holetransport layer and electron transport layer, so that the OLED devicehas a small driving voltage. Furthermore, the compound, used as the hostmaterial in the light emitting layer of the OLED device, has hightriplet energy level and glass transition temperature, and good thermalstability, which ensures the efficient transfer of energy from the hostmaterial to the guest material and prevents the crystallization of thematerial molecules of the light emitting layer.

The compound of the present invention has a high singlet energy level,ensuring efficient energy transfer from the host material to the guestmaterial; and has a small difference between the singlet (

E_(S1)) and triplet energy level (

E_(T1)), which promotes the reverse intersystem crossing of tripletexcitons to singlet excitons. Moreover, the high reverse intersystemcrossing (RISC) rate from the triplet state T1 to the singlet state S1of the hot material can suppress the Dexter energy transfer (DET) fromthe host material to the luminescent dye, promote the FÖrster energytransfer, and reduce the exciton loss generated during the Dexter energytransfer (DET), thus avoiding the efficiency roll-off of the organiclight-emitting device and improving the external quantum efficiency ofthe device, thereby achieving a high device efficiency.

BRIEF DESCRIPTION OF THE DRAWINGS

In order to more clearly explain the technical solutions in the specificembodiments of the present invention or in the prior art, the drawingsused in the description of the specific embodiments or the prior artwill be briefly described below. Obviously, the drawings depicted beloware merely some embodiments of the present invention, and those skilledin the art can obtain other drawings based on these drawings without anycreative efforts.

FIG. 1 is a schematic structural view of an organic light emittingdevice according to Examples 1 to 11 and Comparative Examples 1 to 2 ofthe present invention.

LIST OF REFERENCE NUMERALS

-   -   1—anode, 2—hole injection layer, 3—hole transport layer,        4—organic light-emitting layer, 5—electron transport layer,        6—electron injection layer, 7—cathode.

DETAILED DESCRIPTION

The following examples are provided for better understanding of thepresent invention, which however are not restricted to the preferredembodiments, and not intended to limit the disclosure and protectionscope of the present invention. Products that are the same as or similarto the present invention obtained by any skilled person with thesuggestion of the present invention or by combining the presentinvention with other features in the prior art will fall within theprotection scope of the present invention.

Where no specific experimental steps or conditions are indicated in theexamples, the operation or conditions in the conventional experimentalprocedures described in the literatures in the art are followed. Thereagents or instruments for which no manufacturers are noted are allcommon reagents and products commercially available from the market.

Example 1

This example provides a route for synthesizing a fused polycycliccompound 10.

The compound 10 was prepared through a method comprising specificallythe following steps.

1) Synthesis of intermediate 1-10: To a three-neck flask, acetic acid(500 mL), and then the compound N3 (72.0 g, 0.20 mol) were added, andthen 65 wt % concentrated nitric acid (20.3 g, 0.21 mol) was addeddropwise at 0° C., and then stirred at 0° C. for 2 hrs. The reactionsolution was poured into iced water (800 mL), neutralized with sodiumhydroxide to pH=6-7, and then extracted with ethyl acetate (500 mL×2).The organic phases were combined, washed with saturated brine (200ml×2), and dried over sodium sulfate. The organic phase was rotary driedto obtain a product (78.2 g). The product was purified by columnchromatography (PE:EA=20:1-5:1) to obtain the intermediate 1-10 (63.5 g,yield 78.4%).

2) Synthesis of intermediate 2-10: To a three-neck flask, theintermediate 1-10 (40.5 g, 0.10 mol), the compound N4 (29.3 g, 0.10mol), potassium carbonate (27.6 g, 0.20 mol), and tetrahydrofuran-water(tetrahydrofuran/water volume ratio 3:1, 400 mL) were added.Tetrakis(triphenylphosphine)palladium (1.0 g) was then added under anitrogen atmosphere. Subsequently, the reaction was heated to 75° C. andstirred for 4 hrs under a nitrogen atmosphere. The reaction solution wascooled, taken up in water (200 mL), and extracted with ethyl acetate(200 mL×2). The organic phase was rotary dried to obtain a crudeproduct. The crude product was purified by column chromatography(PE:EA=10:1−5:1), to obtain the intermediate 2-10 (38.9 g, yield 74%).

3) Synthesis of intermediate 3-10: The intermediate 2-10 (26.3 g, 0.050mol) was added to acetic acid (200 mL), and then iron powder (14 g, 0.25mol) was added, and stirred at room temperature for 2 hrs. The ironpowder was filtered off, and the acetic acid was removed by rotarydrying, to obtain a crude product. The crude product was purified bycolumn chromatography (PE:EA=5:1−3:1), to obtain the intermediate 3-10(19.7 g, yield 91.2%).

4) Synthesis of intermediate 4-10: To a three-neck flask, theintermediate 3-10 (13.0 g, 0.030 mol), xylene (120 mL), a 10 wt %tri-tert-butylphosphine solution in xylene (6.0 g, 4 mol %, where in thetri-tert-butylphosphine solution in xylene, tri-tert-butylphosphine wasa solute and xylene was a solvent), and sodium tert-butoxide (5.77 g,0.060 mol) were added. Pd₂(dba)₃ (300 mg, 2.0 mol) was then added undera nitrogen atmosphere. Subsequently, the reaction was heated to 140° C.and stirred for 4 hrs under a nitrogen atmosphere. The reaction solutionwas cooled to room temperature, and xylene was removed by rotary drying.The residue was directly purified by column chromatography(PE:EA=5:1−2:1), to obtain the intermediate 4-10 (9.7 g, yield 77.8%).

5) Synthesis of compound 10: To a three-neck flask, the intermediate4-10 (8.3 g, 0.020 mol), the compound N1 (7.2 g, 0.030 mol), sodiumtert-butoxide (3.85 g, 0.040 mol), xphos (400 mg), and xylene (60 mL)were added. Tetrakis(triphenylphosphine)palladium (200 mg) was thenadded under a nitrogen atmosphere. Subsequently, the reaction was heatedto 140° C. and stirred for 4 hrs under a nitrogen atmosphere. Thereaction solution was cooled, and the organic phase was rotary dried.The residue was purified by column chromatography (PE:EA=4:1−2:1) toobtain a crude product, which was slurried three times each in xyleneand tetrahydrofuran (100 mL×6), to obtain the compound 10 (6.9 g, yield56%).

Element analysis: (C₄₃H₂₈DN₃S) calculated: C, 83.20; H, 4.87; N, 6.77;S, 5.16. found: C, 83.23; H, 4.86; N, 6.76; S, 5.15; HRMS (ESI) m/z(M⁺): calculated: 620.2145. found: 620.2151.

Example 2

This example provides a route for synthesizing a fused polycycliccompound 11.

The compound 11 was prepared through a method comprising specificallythe following steps.

1) Synthesis of intermediate 1-11: The synthesis method was the same asthat for the intermediate 1-10, except that the compound N5 (72 g, 0.2mol) was used in place of the compound N3, to obtain the intermediate1-11 (63.2 g, yield 78%).

2) Synthesis of intermediate 2-11: The synthesis method was the same asthat for the intermediate 2-10, except that the intermediate 1-11 (40.49g, 0.1 mol) was used in place of the intermediate 1-10, and the compoundN2 (30.9 g, 0.1 mol) was used in place of the compound N4 to obtain theintermediate 2-11 (40.2 g, yield 74.1%).

3) Synthesis of intermediate 3-11: The synthesis method was the same asthat for the intermediate 3-10, except that the intermediate 2-11 (27.1g, 0.05 mol) was used in place of the intermediate 2-10, to obtain theintermediate 3-11 (20.6 g, yield 91.8%).

4) Synthesis of intermediate 4-11: The synthesis method was the same asthat for the intermediate 4-10, except that the intermediate 3-11 (13.4g, 0.03 mol) was used in place of the intermediate 3-10, to obtain theintermediate 4-11 (9.8 g, yield 75.5%).

5) Synthesis of compound 11: The synthesis method was the same as thatfor the compound 10, except that the intermediate 4-11 (8.64 g, 0.02mol) was used in place of the intermediate 4-10, to obtain the compound11 (8.1 g, yield 64%).

Element analysis: (C₄₄H₂₈D₃N₃S) calculated: C, 82.99; H, 5.38; N, 6.60;S, 5.03. found: C, 82.97; H, 5.38; N, 6.61; S, 5.03; HRMS (ESI) m/z(M⁺): calculated: 636.2427. found: 636.2433.

Example 3

This example provides a route for synthesizing a fused polycycliccompound 14.

The compound 14 was prepared through a method comprising specificallythe following steps.

1) Synthesis of compound N6: The synthesis method was the same as thatfor the intermediate 1-11, except that the compound

was used in place of the compound N5, and the yield was 74%.

The synthesis route for the compound N6 was shown below:

2) Synthesis of intermediate 1-14: A stir bar was placed in a 500 mltwo-neck round-bottom flask, and then a reflux pipe was connected. Next,the two-neck round-bottom flask was dried and filled with nitrogen. Tothe two-neck round-bottom flask, the compound N6 (30.2 g, 1.2 eq., 0.12mol), the compound N7 (27.8 g, 1.0 eq., 0.1 mol), potassium carbonate(27.6 g, 2 eq., 0.2 mol), and tetrahydrofuran-water(tetrahydrofuran/water volume ratio 3:1, 200 mL) were added.Tetrakis(triphenylphosphine)palladium (6 mmol) was then added under anitrogen atmosphere. Subsequently, the reaction was heated to 75° C. andstirred for 4 hrs under a nitrogen atmosphere. The reaction solution wascooled, taken up in water (150 mL), and extracted with ethyl acetate(150 mL×2). The organic phase was rotary dried to obtain a crudeproduct. The crude product was purified by column chromatography(PE:EA=20:1−8:1), to obtain the intermediate 1-14 as a yellow solid(32.9 g, yield 81%).

3) Synthesis of intermediate 2-14: A stir bar was placed in a 500 mltwo-neck round-bottom flask, and then a reflux pipe was connected. Next,the two-neck round-bottom flask was dried and filled with nitrogen. Tothe two-neck round-bottom flask, the intermediate 1-14 (40.6 g, 1 eq.,0.1 mol) and triethyl phosphite (250 mL) were respectively added andstirred at 120° C. for 16 hrs. The reaction solution was cooled, rotarydried to remove the solvent, added with water (200 mL), and thenextracted with ethyl acetate (200 mL×2). The organic phases werecombined, washed with saturated saline, dried over sodium sulfate, androtary dried to obtain a crude product (41.5 g). The crude product waspurified by column chromatography (PE:EA=10:1−5:1), and then rotarydried to obtain the intermediate 2-14 (30.5 g, yield 81.5%).

4) Synthesis of compound 14: A stir bar was placed in a 500 ml two-neckround-bottom flask, and then a reflux pipe was connected. Next, thetwo-neck round-bottom flask was dried and filled with nitrogen. To thetwo-neck round-bottom flask, the compound N1 (24 g, 1 eq., 0.1 mol), theintermediate 2-14 (37.3 g, 1 eq.), tert-BuNa (sodium tert-butoxide, 3eq.), xylene (120 ml), xphos (1 g), and Pd[PPh₃]₄(tetrakis(triphenylphosphine)palladium, 0.05 eq., 5 mmol) wererespectively added. The reaction system was stirred at 140° C. for 5hrs, and then cooled to room temperature after reaction. The reactionsystem was filtered, and the filtrate was concentrated to obtain a crudeproduct. The crude product was purified by chromatography (ethylacetate/hexane, volume ratio 1/10), to obtain the compound 14 (42.2 g,yield 73%).

Element analysis: C₄₀H₂₂DN₃S calculated: C, 83.02; H, 4.18; N, 7.26.found: C, 83.05; H, 4.16; N, 7.25; HRMS (ESI) m/z (M+): calculated:578.1675. found: 578.1681.

Example 4

This example provides a route for synthesizing a fused polycycliccompound 26.

The compound 26 was prepared through a method comprising specificallythe following steps.

1) Synthesis of compound N9: The synthesis method was the same as thatfor the intermediate 1-11, except that the compound

was used in place of the compound N5, and the yield was 73%.

The synthesis route for the compound N9 was shown below:

2) Synthesis of intermediate 1-26: To a three-neck flask, the compoundN9 (81.0 g, 0.20 mol), 2-mercapto-1-naphthaleneboronic acid (thecompound N10, 49.0 g, 0.24 mol), potassium carbonate (55.2 g, 0.40 mol),and tetrahydrofuran-water (tetrahydrofuran/water volume ratio 3:1, 600mL) were added. Tetrakis(triphenylphosphine)palladium (0.01 mol) wasthen added under a nitrogen atmosphere. Subsequently, the reaction washeated to 75° C. and stirred for 4 hrs under a nitrogen atmosphere. Thereaction solution was cooled, taken up in water (300 mL), and extractedwith ethyl acetate (300 mL×2). The organic phase was rotary dried toobtain a crude product. The crude product was purified by columnchromatography (PE:EA=8:1−3:1), to obtain the intermediate 1-26 (61.3 g,yield 70%).

3) Synthesis of intermediate 2-26: The intermediate 1-26 (43.8 g, 0.10mol) was added to acetic acid (300 mL), and then iron powder (28 g, 0.50mol) was added, and stirred at room temperature for 2 hrs. The ironpowder was filtered off, and the acetic acid was removed by rotarydrying, to obtain a crude product (62 g). The crude product was purifiedby column chromatography (PE:EA=5:1−2:1), to obtain the intermediate2-26 (36.8 g, yield 90.2%).

4) Synthesis of intermediate 3-26: The intermediate 2-26 (20.4 g, 0.050mol) was dissolved in DMF (100 mL) in a three-neck flask, and thenpotassium bromide (1.19 g, 0.010 mol) was added and reacted at 110° C.for 12 hrs. The reaction solution was cooled, rotary dried to remove thesolvent, diluted with water (100 mL), and extracted with ethyl acetate(100 mL×2). The organic phases were combined, washed with saturatedsaline (100 mL×2), and dried over sodium sulfate. The solvent wasremoved by rotary dried, and a crude product 3-26 was obtained, whichwas purified by column chromatography (PE:EA=3:1−1:1), and rotary driedto obtain the intermediate 3-26 (13.0 g, yield 64%).

5) Synthesis of compound 26: To a three-neck flask, the intermediate3-26 (8.1 g, 0.020 mol), the compound N1 (7.2 g, 0.030 mol), sodiumtert-butoxide (3.85 g, 0.040 mol), xphos (400 mg), and xylene (60 mL)were added. Tetrakis(triphenylphosphine)palladium (1 mmol) was thenadded under a nitrogen atmosphere. Subsequently, the reaction was heatedto 140° C. and stirred for 4 hrs under a nitrogen atmosphere. Thereaction solution was cooled, and the organic phase was rotary dried.The residue was purified by column chromatography (PE:EA=4:1−2:1) toobtain a crude product of the compound 26, which was slurried threetimes each in xylene and tetrahydrofuran (80 mL×6), to obtain thecompound 26 (7.8 g, yield 64%).

Element analysis: C₄₀H₂₂DN₃S₂ calculated: C, 78.66; H, 3.96; N, 6.88.found: C, 78.64; H, 3.96; N, 6.89; HRMS (ESI) m/z (M+): calculated:610.1396. found: 610.1400.

Example 5

This example provides a route for synthesizing a fused polycycliccompound 74.

The compound 74 was prepared through a method comprising specificallythe following steps.

1) Synthesis of compound N11: The synthesis method was the same as thatfor the intermediate 1-11, except that the compound

was used in place of the compound N5, and the yield was 70%.

The synthesis route for the compound N11 was shown below:

2) Synthesis of intermediate 1-74: To a three-neck flask, the compoundN11 (39.0 g, 0.10 mol), the compound N12 (21.7 g, 0.10 mol), potassiumcarbonate (27.6 g, 0.20 mol), and tetrahydrofuran-water(tetrahydrofuran/water volume ratio 3:1, 400 mL) were added.Tetrakis(triphenylphosphine)palladium (1.0 g) was then added under anitrogen atmosphere. Subsequently, the reaction was heated to 75° C. andstirred for 4 hrs under a nitrogen atmosphere. The reaction solution wascooled, taken up in water (200 mL), and extracted with ethyl acetate(200 mL×2). The organic phase was rotary dried to obtain a crudeproduct. The crude product was purified by column chromatography(PE:EA=20:1−10:1), to obtain the intermediate 1-74 (32.2 g, yield 74%).

3) Synthesis of intermediate 2-74: To a three-neck flask, theintermediate 1-74 (21.7 g, 0.05 mol) was added, isopropanol (200 mL) wasadded to dissolve the intermediate, and then titania (8.0 g, 0.10 mol)was added. Under a nitrogen atmosphere, the reaction was continued for16 hrs under UV irradiation. The solvent was rotary dried, and theresidue was purified by column chromatography (PE:EA=15:1−5:1) to obtainthe intermediate 2-74 (12.6 g, yield 68%).

4) Synthesis of compound 74: To a three-neck flask, the intermediate2-74 (7.4 g, 0.02 mol) was added, and then anhydrous tetrahydrofuran (50mL) was added, and cooled to −78° C. Phenyl lithium (20 mL, 0.02 mol)was added dropwise and stirred for 2 hrs while the temperature wasmaintained at −78° C. Then a solution of the compound N1 (4.8 g, 0.02mol) in tetrahydrofuran (30 mL) was added dropwise. After the addition,the mixture was incubated at −78° C. for 2 hrs and then allowed to warmto room temperature overnight. The reaction solution was quenched withwater (100 mL), extracted with ethyl acetate (100 mL×2), washed withsaturated saline, dried over sodium sulfate, and rotary dried to obtaina crude product, which was purified by column chromatography(PE:EA=7:1−3:1), to obtain the compound 74 (8.2 g, yield 63%).

Element analysis: C₄₆H₂₇DN₄₀ calculated: C, 84.51; H, 4.47; N, 8.57.found: C, 84.54; H, 4.48; N, 8.58; HRMS (ESI) m/z (M+): calculated:653.2326. found: 653.2331.

Example 6

This example provides a route for synthesizing a fused polycycliccompound 76.

The compound 76 was prepared through a method comprising specificallythe following steps.

1) Synthesis of compound N13: The synthesis method was the same as thatfor the intermediate 1-11, except that the compound

was used in place of the compound N5, and the yield was 71%.

The synthesis route for the compound N13 was shown below:

2) Synthesis of intermediate 1-76: The synthesis method was the same asthat for the intermediate 1-74, except that the compound N14 (21.8 g, 1eq., 0.1 mol) was used in place of the compound N12, to obtain theintermediate 1-76 (32.1 g, yield 71%).

3) Synthesis of intermediate 2-76: The synthesis method was the same asthat for the intermediate 2-74, except that the intermediate 1-76 (22.6g, 0.05 mol) was used in place of the intermediate 1-74, to obtain theintermediate 2-76 (11.6 g, yield 60%).

4) Synthesis of compound 76: The synthesis method was the same as thatfor the compound 74, except that the intermediate 2-76 (7.76 g, 0.02mol) was used in place of the intermediate 2-74, to obtain the compound76 (7.9 g, yield 59%).

Element analysis: C₄₆H₂₆D₂N₄S calculated: C, 82.36; H, 4.51; N, 8.35; S,4.78. found: C, 82.39; H, 4.50; N, 8.34; S, 4.77; HRMS (ESI) m/z (M+):calculated: 670.2160. found: 670.2165.

Example 7

This example provides a route for synthesizing a fused polycycliccompound 92.

The compound 92 was prepared through a method comprising specificallythe following steps.

1) Synthesis of compound N15: The synthesis method was the same as thatfor the intermediate 2-26, except that

was used in place of the compound N9, and

was used in place of the compound N10

and the final yield was 52%.

The synthesis route for the compound N15 was shown below:

2) Synthesis of intermediate 2-92: To a three-neck flask, the compoundN15 (75.1 g, 0.20 mol), and then benzene (500 mL) and anhydrousphosphorus trichloride (27.5 g, 0.2 mol) were added, and refluxed for 16hrs under a nitrogen atmosphere. The reaction solution was cooled,rotary dried to remove the benzene, and then added with anhydrousaluminum trichloride (3.1 g, 0.02 mol). The reaction mixture was reactedat 180° C. for 5 hrs, cooled, and purified by column chromatography(PE:EA=5:1−3:1), to obtain the intermediate 2-92 (61.4 g, yield 69.8%).

3) Synthesis of intermediate 3-92: To a three-neck flask, theintermediate 2-92 (44.0 g, 0.10 mol), and then anhydrous tetrahydrofuran(300 mL) were added. Under a nitrogen atmosphere, the phenyl grignardreagent (150 mL, 0.30 mol) was added dropwise at 0° C. After addition,the system was stirred at room temperature for 12 hrs, refluxed for 2hrs, cooled, poured into iced water (300 mL), and adjusted to a neutralpH with 5 wt % hydrochloric acid. The reaction solution was extractedwith dichloromethane (200 mL×2), and the organic phase was washed withsaturated saline (200 mL), dried over sodium sulfate, and rotary driedto obtain a crude product. The crude product was recrystallized indiethyl ether:dichloromethane (volume ratio 1:1, 400 mL), to obtain theintermediate 3-92 (31.1 g, yield 64.6%).

4) Synthesis of compound 92: To a three-neck flask, the intermediate3-92 (9.6 g, 0.020 mol), the compound N1 (7.2 g, 0.030 mol), sodiumtert-butoxide (3.9 g, 0.040 mol), xphos (400 mg), and xylene (60 mL)were added. Tetrakis(triphenylphosphine)palladium (200 mg) was thenadded under a nitrogen atmosphere. Subsequently, the reaction was heatedto 140° C. and stirred for 4 hrs under a nitrogen atmosphere. Thereaction solution was cooled, and the organic phase was rotary dried.The residue was purified by column chromatography (PE:EA=8:1−4:1) toobtain a crude product of the compound 92, which was slurried threetimes each in xylene and tetrahydrofuran (80 mL×6), to obtain thecompound 92 (7.3 g, yield 53.2%).

Element analysis: (C₄₆H₂₇DN₃PS) calculated: C, 80.45; H, 4.26; N, 6.12;S, 4.67. found: C, 80.48; H, 4.26; N, 6.12; S, 4.65; HRMS (ESI) m/z(M+): calculated: 686.1804. found: 686.1799.

Example 8

This example provides a route for synthesizing a fused polycycliccompound 95.

The compound 95 was prepared through a method comprising specificallythe following steps.

1) Synthesis of compound N16: The synthesis method was the same as thatfor the intermediate 2-26, except that the compound

was used in place of the compound N10

and the final yield was 56%.

The synthesis route for the compound N16 was shown below:

2) Synthesis of intermediate 2-95: The synthesis method was the same asthat for the intermediate 2-92, except that the compound N16 (75 g, 0.20mol) was used in place of the compound N15, to obtain the intermediate2-95 (63.0 g, yield 71.8%).

3) Synthesis of intermediate 3-95: The synthesis method was the same asthat for the intermediate 3-92, except that the intermediate 2-95 (43.9g, 0.1 mol) was used in place of the intermediate 2-92, to obtain theintermediate 3-95 (29.4 g, yield 61.2%).

4) Synthesis of compound 95: The synthesis method was the same as thatfor the compound 92, except that the intermediate 3-95 (9.6 g, 0.02 mol)was used in place of the intermediate 3-92, to obtain the compound 95(7.9 g, yield 57.8%).

Element analysis: (C₄₇H₂₇D₃N₃PS) calculated: C, 80.32; H, 4.73; N, 5.98;S, 4.56. found: C, 80.36; H, 4.72; N, 5.96; S, 4.55; HRMS (ESI) m/z(M⁺): calculated: 702.2086. found: 702.2091.

Example 9

This example provides a route for synthesizing a fused polycycliccompound 111.

The compound 111 was prepared through a method comprising specificallythe following steps.

1) Synthesis of intermediate 1-111: To a three-neck flask, the compoundN19 (81.0 g, 0.20 mol), N20 (41.3 g, 0.24 mol), potassium carbonate(55.2 g, 0.40 mol), and tetrahydrofuran-water (tetrahydrofuran/watervolume ratio 3:1, 500 mL) were added.Tetrakis(triphenylphosphine)palladium (2.0 g) was then added under anitrogen atmosphere. Subsequently, the reaction was heated to 75° C. andstirred for 4 hrs under a nitrogen atmosphere. The reaction solution wascooled, and extracted. The organic phase was rotary dried to obtain acrude product. The crude product was purified by column chromatography(PE:EA=10:1−5:1), to obtain the intermediate 1-111 (61 g, yield 75.1%).

2) Synthesis of intermediate 2-111: The intermediate 1-111 (40.6 g, 0.10mol) was added to acetic acid (300 mL), and then iron powder (28 g, 0.50mol) was added, and stirred at room temperature for 2 hrs. The ironpowder was filtered off, and the acetic acid was removed by rotarydrying, to obtain a crude product (50 g). The crude product was purifiedby column chromatography (PE:EA=5:1−3:1), to obtain the intermediate2-111 (34.7 g, yield 92.3%).

3) Synthesis of intermediate 3-111: To a three-neck flask, theintermediate 2-111 (18.8 g, 0.05 mol), phenylboron dichloride (9.5 g,0.06 mol), anhydrous toluene (150 mL), and aluminum trichloride (10.0 g,0.08 mol) were added. Under a nitrogen atmosphere, the mixture wasrefluxed in toluene for 4 hrs, cooled, and filtered. The filtrate waswashed with saturated brine (100 mL), rotary dried, and slurried twicein toluene (100 mL×2), to obtain the intermediate 3-111 (15.2 g, 66%).

4) Synthesis of compound 111: To a three-neck flask, the intermediate3-111 (9.2 g, 0.020 mol), the compound N1 (7.22 g, 0.030 mol), sodiumtert-butoxide (3.9 g, 0.040 mol), xphos (400 mg), and xylene (60 mL)were added. Tetrakis(triphenylphosphine)palladium (200 mg) was thenadded under a nitrogen atmosphere. Subsequently, the reaction was heatedto 140° C. and stirred for 4 hrs under a nitrogen atmosphere. Thereaction solution was cooled, and the organic phase was rotary dried.The residue was purified by column chromatography (PE:EA=4:1−2:1) toobtain a crude product, which was slurried three times each in xyleneand tetrahydrofuran (80 mL×6), to obtain the compound 111 (8.1 g, yield60.6%).

Element analysis: (C₄₆H₂₇DBN₃S) calculated: C, 82.88; H, 4.38; N, 6.30;S, 4.81. found: C, 82.90; H, 4.38; N, 6.29; S, 4.80; HRMS (ESI) m/z(M⁺): calculated: 666.2160. found: 666.2166.

Example 10

This example provides a route for synthesizing a fused polycycliccompound 107.

The compound 107 was prepared through a method comprising specificallythe following steps.

1) Synthesis of compound N17: The synthesis method was the same as thatfor the intermediate 1-11, except that the compound

was used in place of the compound N5, and the yield was 73%.

2) Synthesis of intermediate 1-107: The synthesis method was the same asthat for the intermediate 1-111, except that the compound N17 (77.8 g,0.20 mol) was used in place of the compound N19, and the compound N18was used in place of the compound N20, to obtain the intermediate 1-107(56.8 g, yield 73.0%).

3) Synthesis of intermediate 2-107: The synthesis method was the same asthat for the intermediate 2-111, except that the intermediate 1-107(38.9 g, 0.01 mol) was used in place of the intermediate 1-111, toobtain the intermediate 2-107 (33.5 g, yield 93.2%).

4) Synthesis of intermediate 3-107: The synthesis method was the same asthat for the intermediate 3-111, except that the intermediate 2-107(18.0 g, 0.05 mol) was used in place of the intermediate 2-111, toobtain the intermediate 3-107 (14.9 g, yield 67%).

5) Synthesis of compound 107: The synthesis method was the same as thatfor the compound 111, except that the intermediate 3-107 (8.9 g, 0.02mol) was used in place of the intermediate 3-111, to obtain the compound107 (8.2 g, yield 63.0%).

Element analysis: (C₄₆H₂₇DBN₃₀) calculated: C, 84.93; H, 4.49; N, 6.46.found: C, 84.97; H, 4.49; N, 6.45; HRMS (ESI) m/z (M⁺): calculated:650.2388. found: 650.2393.

Example 11

This example provides a route for synthesizing a fused polycycliccompound 133.

The preparation method of the compound 133 was the same as that for thecompound 14, except that the intermediate 2 was used in place of theintermediate 2-14, and the compound 133 was obtained with a yield of66%.

Element analysis: C₄₀H₂₃N₃S calculated: C, 83.16; H, 4.01; N, 7.27; S,5.55. found: C, 83.19; H, 4.01; N, 7.25; S, 5.54; HRMS (ESI) m/z (M+):calculated: 577.1613. found: 577.1619.

Device Example 1

This example provides an organic light-emitting device, which includes,from bottom to top, an anode 1, a hole injection layer 2, a holetransport layer 3, a light emitting layer 4, an electron transport layer5, an electron injection layer 6 and a cathode 7 stacked in sequence.The device is configured to have a particular structure of ITO/holeinjection layer (HIL) (30 nm)/hole transport layer (HTL) (40 nm)/organiclight-emitting layer (compound 10 doped with compound RD) (40nm)/electron transport layer (ETL) (40 nm)/electron injection layer(EIL/LiF) (1 nm)/cathode (Al) (150 nm) as shown in FIG. 1.

In the organic light-emitting device, the material of the anode 1 isITO.

The material of the hole injection layer 2 is the compound HAT(CN)₆having a structure below:

The material of the hole transport layer 3 is the compound NPB having astructure below:

The organic light emitting layer 4 is formed by blending a host materialand a guest material, where the host material is the compound 10, andthe guest material is the compound RD; the host material and the guestmaterial are blended at a weight ratio of 100:5; and the compound RD hasa chemical structure shown below:

The material of the electron transport layer 5 is the compound CBPhaving a structure below:

The material of the electron injection layer 6 is formed by the compoundBCP having a structure below, blended with the electron injectionmaterial LiF, where BCP and LiF are blended at a weight ratio of 100:3:

The material of the cathode 7 is the metal Al.

The organic light emitting device was fabricated through a processcomprising the following steps.

1) Cleaning of Substrate:

A glass substrate coated with an ITO transparent electrode wasultrasonically treated in a commercial detergent (Yokohama ChemicalTechnology (Changzhou) Co., Ltd., with an ethylene glycol solvent of ≤10wt %, and triethanolamine of ≤1 wt %), rinsed in deionized water,ultrasonicated in a mixed solvent of acetone:ethanol (volume ratio 1:1)to remove the oil, baked in a clean environment to completely remove themoisture, and then cleaned with ultraviolet light and ozone.

2) Fabrication of Organic Layer and Cathode:

The glass substrate with the anode layer was placed in a vacuum chamberwhich was then evacuated to 1×10⁻⁶ to 2×10⁻⁴ Pa. HAT(CN)₆ was deposited,as a hole injection layer, onto the anode film, where the depositionrate was 0.1 nm/s, and the film thickness deposited was 30 nm.

A hole transport layer was deposited on the hole injection layer, wherethe deposition rate was 0.1 nm/s, and the film thickness deposited was40 nm.

An organic light-emitting layer was deposited on the hole transportlayer. The fabrication process was specifically as follows. Aluminescent host material and guest material were deposited under vacuumby means of co-deposition, where the host material was deposited at arate of 0.1 nm/s, the guest material was deposited at a rate of 0.005nm/s, and the total film thickness deposited was 40 nm.

An electron transport layer was deposited on the organic light-emittinglayer under vacuum, where the deposition rate was 0.1 nm/s, and thetotal film thickness deposited was 40 nm.

An electron injection layer was deposited on the electron transportlayer under vacuum, where the deposition rate was 0.05 nm/s, and thetotal film thickness deposited was 1 nm.

Al was deposited on the electron injection layer, where the depositionrate was 0.1 nm/s, and the total film thickness deposited was 150 nm.

Device Example 2

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 11.

Device Example 3

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 14.

Device Example 4

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 26.

Device Example 5

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 74.

Device Example 6

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 76.

Device Example 7

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 92.

Device Example 8

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 95.

Device Example 9

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 111.

Device Example 10

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 107.

Device Example 11

This example provides an organic light-emitting device, which differsfrom the organic light-emitting device provided in Device Example 1 inthat the host material in the light emitting layer is the compound 133.

Comparative Example 1

This comparative example provides an organic light-emitting device,which differs from the organic light-emitting device provided in DeviceExample 1 in that the host material in the light emitting layer is thecompound E-1.

Comparative Example 2

This comparative example provides an organic light-emitting device,which differs from the organic light-emitting device provided in DeviceExample 1 in that the host material in the light emitting layer is thecompound E-2.

Test Example 1

1. Determination of Thermal Deposition Temperature and Glass TransitionTemperature

Determination of thermal decomposition temperature of the compound: Thethermal decomposition temperature (Td) of the material of the presentinvention was determined by using a thermogravimetric analyzer (TGA, USTA TGA55) in a temperature range from room temperature to 600° C. at aheating rate of 10° C./min, under nitrogen atmosphere. A temperature atwhich 5 wt % loss occurs is defined as the decomposition temperature.

Determination of glass transition temperature of the compound: The glasstransition temperature (Tg) of the material according to the presentinvention was tested by differential scanning calorimetery (DSC, US TADSC250) in a temperature range from room temperature to 600° C. at aheating rate of 10° C./min and a cooling rate of 10° C./min undernitrogen atmosphere, where two cycles of heating and cooling wereperformed.

2. Test of LUMO and HOMO Level

The HOMO and LUMO level of the material according to the presentinvention was tested by cyclic voltammetry (CV, CHI-600E from ShanghaiChenhua Instrument Co., Ltd.) using an electrochemical workstation withplatinum (Pt) as a counter electrode and silver/silver chloride(Ag/AgCl) as a reference electrode. Under a nitrogen atmosphere, thetest was carried out at a scan rate of 100 mV/s in an electrolytesolution containing 0.1 M tetrabutylammonium hexafluorophosphate indichloromethane, and the potential was calibrated by ferrocene, in whichthe potential of ferrocene was set to an absolute energy level undervacuum of −4.8 eV:

HOMO=−[E _(onset) ^(ox) −E _(Fc/Fc+)+4.8]eV.

LUMO=−[E _(onset) ^(red) −E _(Fc/Fc+)+4.8]eV.

Test of triplet energy level: Toluene was used as a solvent, thecompound to be tested was formulated into a solution (with aconcentration of 2*10⁻⁵ mol/L), and the solution was tested at −78° C.using a fluorescence spectrophotometer (Hitachi F-4600). E_(T1) (eV)represents the triplet energy level of the compound, which is calculatedusing a formula below:

E _(T1)=1240/λ

where λ is the shortest ultraviolet/visible absorption wavelength.

The test results are shown in Table 1.

TABLE 1 Compound 10 11 14 26 74 76 92 95 111 107 T_(d) (° C.) 394 395386 385 378 373 375 373 382 381 Tg (° C.) 123 124 140 133 132 128 124127 124 112 HOMO (eV) −5.2 −5.2 −5.2 −5.3 −5.1 −5.1 −5.1 −5.0 −5.3 −5.2LUMO (eV) −1.9 −1.9 −2.2 −2.1 −2.1 −2.2 −2.0 −2.2 −1.9 −2.0 E_(T1) (eV)2.08 2.10 2.28 2.12 2.13 2.09 2.11 2.07 2.09 2.13

The results shown in Table 1 show that the fused polycyclic compoundprovided in the present invention has a high thermal decompositiontemperature, which ensures that the host material formed therefrom canmaintain excellent thermal stability in the device, making the deviceunlikely to deteriorate due to decomposition during the fabricationprocess. The HOMO level and LUMO level of the fused polycyclic compoundprovided in the present invention are matched with the adjacenttransport layer, so that the OLED device has a small driving voltage.

In addition, the fused polycyclic compound provided in the presentinvention has a high singlet energy level, ensuring the efficient energytransfer from the host material to the guest material.

Test Example 2

Instruments: The current, voltage, brightness, and lifetime of thedevice were tested synchronously using PR 650 scanning spectroradiometer and Keithley K2400 digital source meter.

Test conditions: current density 10 mA/cm²; temperature 25° C.

The organic light-emitting devices provided in Device Examples 1-11 andComparative Examples 1-2 were tested. The results are shown in Table 2.

TABLE 2 Current Current Device Host density/ efficiency/ Chrominance/Example material Voltage/V mA/cm² cd/A CIE (X, Y) Lifetime/hr 1 10 4.010 40 (0.66, 0.31) 130 2 11 4.0 10 39 (0.66, 0.31) 130 3 14 4.2 10 42(0.66, 0.31) 145 4 26 4.3 10 43 (0.66, 0.31) 132 5 74 4.2 10 44 (0.67,0.31) 133 6 76 4.2 10 46 (0.66, 0.31) 136 7 92 4.2 10 45 (0.68, 0.31)131 8 95 4.3 10 47 (0.66, 0.30) 130 9 111 4.2 10 44 (0.68, 0.31) 132 10107 4.1 10 43 (0.68, 0.30) 133 11 133 4.4 10 40 (0.67, 0.31) 130Comparative E-1 4.3 10 37 (0.66, 0.31) 127 Example 1 Comparative E-2 4.410 36 (0.66, 0.31) 113 Example 2

The organic light-emitting devices provided in Device Examples 1-11 andComparative Examples 1-2 were tested. The results are shown in Table 2.Compared with the device provided in the comparative examples, the OLEDdevices provided in the examples of the present invention has loweroperating voltage, higher current efficiency, and longer lifetime,indicating that the fused polycyclic compound provided in the presentinvention, when used as a luminescent host material in an OLED device,can greatly improve the luminescence efficiency, reduce the drivingvoltage, extend the lifetime, and increase the performance of the OLEDdevice. Notably, the inventors find through research that when thephenyl ring in the structure of the fused polycyclic compound providedin the present invention is not attached, at positions 1 and 2, 2 and 3,or 3 and 4, to

to form a fused ring sharing the same side, the current efficiency andlifetime of the device are seriously affected.

Apparently, the above-described embodiments are merely examples providedfor clarity of description, and are not intended to limit theimplementations of the present invention. Other variations or changescan be made by those skilled in the art based on the above description.The embodiments are not exhaustive herein. Obvious variations or changesderived therefrom also fall within the protection scope of the presentinvention.

What is claimed is:
 1. A fused polycyclic compound, having a structureshown below:

wherein the phenyl ring is attached to

at positions 1 and 2, positions 2 and 3, or positions 3 and 4 to form afused ring sharing the same side, in which “

” and “

” denotes the points of attachment; where when the phenyl ring isattached to

at positions 3 and 4 to form a fused ring sharing the same side, theGeneral Formula IV has a structure below:

when the phenyl ring is attached to

at positions 2 and 3 to form a fused ring sharing the same side, theGeneral Formula IV has a structure below:

and when the phenyl ring is attached to

at positions 1 and 2 to form a fused ring sharing the same side, theGeneral Formula IV has a structure below:

T¹ is independently selected from a single bond, NR⁵, S, O, BR, PR, andC(R)₂, in which R¹⁵ is the same or different, and is each independentlyselected from methyl, deuterated methyl, phenyl, deuterated phenyl,biphenylyl, deuterated biphenylyl, naphthalenyl, and deuteratednaphthalenyl; at least one of T² and T³ is a single bond, when T² is asingle bond, T³ is S or O, and when T³ is a single bond, T² is S or O;and R¹-R¹⁴ are the same or different, and are each independentlyselected from hydrogen, deuterium, methyl, deuterated methyl, phenyl,deuterated phenyl, and deuterated methyl substituted phenyl.
 2. Thefused polycyclic compound according to claim 1, wherein R¹-R¹⁴ are thesame or different, at least one of which is one selected from deuterium,deuterated methyl, deuterated phenyl, and deuterated methyl substitutedphenyl.
 3. The fused polycyclic compound according to claim 1, whereinR¹-R⁴ are the same or different, and at least one of them is hydrogen;and/or R⁵-R⁸ are the same or different, and at least one of them ishydrogen; and/or R¹¹-R¹⁴ are the same or different, and at least one ofthem is hydrogen.
 4. The fused polycyclic compound according to claim 1,wherein when T² is a single bond, T³ is S or O; and preferably, when T²is a single bond, T³ is S.
 5. The fused polycyclic compound according toclaim 1, having a structure shown below:


6. The fused polycyclic compound according to claim 1, having any one ofthe molecular structures shown below:


7. A method for preparing a fused polycyclic compound according to claim1, wherein when T¹ is selected from C(R¹⁵)₂, that is, the fusedpolycyclic compound has a structure of General Formula IV-1, and T⁴ isselected from Cl C(R¹⁵)₂ or Br C(R¹⁵)₂, the preparation methodcomprises: subjecting the compound of Formula (E) used as a raw materialto a cyclization reaction in the presence of a catalyst to obtain anintermediate compound (F); and coupling the intermediate compound (F) tothe compound of Formula (G) in the presence of a catalyst, to obtain thecompound of General Formula IV-1; and the route for preparing thecompound of General Formula IV-1 is shown below:

alternatively, when T¹ is selected from BR¹⁵, that is, the fusedpolycyclic compound has a structure of General Formula IV-2, and T⁴ isselected from hydrogen, the preparation method comprises: reacting thecompound of Formula (E) used as a raw material with the compound ofFormula (H) in the presence of a catalyst to obtain an intermediatecompound (J); and coupling the intermediate compound (J) to the compoundof Formula (G) in the presence of a catalyst, to obtain the compound ofGeneral Formula IV-2; and the route for preparing the compound ofGeneral Formula IV-2 is shown below:

alternatively, when T¹ is selected from O, that is, the fused polycycliccompound has a structure of General Formula IV-3, and T⁴ is selectedfrom hydroxyl, the preparation method comprises: reacting the compoundof Formula (E) used as a raw material in the presence of a catalyst toobtain an intermediate compound (K); and coupling the intermediatecompound (K) to the compound of Formula (G) in the presence of acatalyst, to obtain the compound of General Formula IV-3; and the routefor preparing the compound of General Formula IV-3 is shown below:

alternatively, when T¹ is selected from S, that is, the fused polycycliccompound has a structure of General Formula IV-4, and T⁴ is selectedfrom mercapto, the preparation method comprises: reacting the compoundof Formula (E) used as a raw material in the presence of a catalyst toobtain an intermediate compound (K-1); and coupling the intermediatecompound (K-1) to the compound of Formula (G) in the presence of acatalyst, to obtain the compound of General Formula IV-4; and the routefor preparing the compound of General Formula IV-4 is shown below:

alternatively, when T¹ is selected from PR, that is, the fusedpolycyclic compound has a structure of General Formula IV-5, and T⁴ isselected from hydrogen, the preparation method comprises: reacting thecompound of Formula (E) used as a raw material in the presence of acatalyst to obtain an intermediate compound (L); reacting theintermediate compound (L) in the presence of a catalyst to obtain anintermediate compound (M); coupling the intermediate compound (M) to thecompound of Formula (N) in the presence of a catalyst to obtain anintermediate compound (0); and coupling the intermediate compound (O) tothe compound of Formula (G) in the presence of a catalyst, to obtain thecompound of General Formula IV-5; and the route for preparing thecompound of General Formula IV-5 is shown below:

alternatively, when T¹ is selected from NR¹⁵, that is, the fusedpolycyclic compound has a structure of General Formula IV-6, and T⁴ isselected from nitro, the preparation method comprises: reacting thecompound of Formula (D) used as a raw material in the presence of acatalyst to obtain an intermediate compound (P); and reacting theintermediate compound (P) with the compound of Formula (Q) and then thecompound of Formula (G), to obtain the compound of General Formula IV-6;and the route for preparing the compound of General Formula IV-6 isshown below:

alternatively, when T¹ is selected from a single bond, that is, thefused polycyclic compound has a structure of General Formula IV-7, thepreparation method comprises: reacting the compound of Formula (R) usedas a raw material with the compound of Formula (S) in the presence of acatalyst to obtain an intermediate compound (T); subjecting theintermediate compound (T) to a cyclization reaction in the presence of acatalyst to obtain an intermediate compound (U); and coupling theintermediate compound (U) to the compound of Formula (G) in the presenceof a catalyst, to obtain the compound of General Formula IV-7; and theroute for preparing the compound of General Formula IV-7 is shown below:

where W is selected from fluoro, chloro, bromo, or iodo.
 8. The methodfor preparing a fused polycyclic compound according to claim 7, whereinthe compound of Formula (E) is prepared through a method comprising:nitrifying the compound of Formula (A) used as a starting raw materialin the presence of a catalyst to obtain an intermediate compound (B);coupling the intermediate compound (B) to the compound of Formula (C) inthe presence of a catalyst to obtain an intermediate compound (D); andreducing the intermediate compound (D) in the presence of a catalyst, toobtain the compound of Formula E; and the route for preparing thecompound of Formula E is shown below:


9. An electronic device, comprising any one or a combination of at leasttwo of the fused polycyclic compounds according to claim 1, whereinpreferably, the electronic device is any one of an organic lightemitting diode, an organic field effect transistor, an organic thin filmtransistor, an organic light emitting transistor, an organic integratedcircuit, an organic solar cell, an organic field quenching device, alight emitting electrochemical cell, an organic laser diode or anorganic photoreceptor.
 10. The electronic device according to claim 9,which is an organic light emitting device comprising an anode, acathode, and an organic thin film layer between the anode and thecathode, wherein the organic thin film layer comprises any one or acombination of at least two of the fused polycyclic compounds accordingto claim 1, wherein preferably, the organic thin film layer comprises alight-emitting layer, and also any one or a combination of at least twoof a hole injection layer, a hole transport layer, a hole blockinglayer, an electron transport layer, an electron injection layer, anelectron blocking layer, and a charge transport layer, wherein thelight-emitting layer comprises any one or a combination of at least twoof the fused polycyclic compounds according to claim 1; and preferably,the light-emitting layer comprises a host material and a guest material;and the host material in the light-emitting layer comprises any one or acombination of at least two of the fused polycyclic compounds accordingto claim
 1. 11. A display device, comprising an electronic deviceaccording to claim
 9. 12. A lighting device, comprising an electronicdevice according to claim
 9. 13. The fused polycyclic compound accordingto claim 2, wherein R¹-R⁴ are the same or different, and at least one ofthem is hydrogen; and/or R⁵-R⁸ are the same or different, and at leastone of them is hydrogen; and/or R¹¹-R¹⁴ are the same or different, andat least one of them is hydrogen.
 14. The fused polycyclic compoundaccording to claim 2, wherein when T² is a single bond, T³ is S or O;and preferably, when T² is a single bond, T³ is S.
 15. The fusedpolycyclic compound according to claim 3, wherein when T² is a singlebond, T³ is S or O; and preferably, when T² is a single bond, T³ is S.16. The fused polycyclic compound according to claim 2, having astructure shown below:


17. The fused polycyclic compound according to claim 3, having astructure shown below:


18. The fused polycyclic compound according to claim 4, having astructure shown below:


19. The fused polycyclic compound according to claim 2, having any oneof the molecular structures shown below:


20. The fused polycyclic compound according to claim 3, having any oneof the molecular structures shown below: